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Synthesis 2015; 47(06): 817-826
DOI: 10.1055/s-0034-1379887
DOI: 10.1055/s-0034-1379887
paper
Tricyclic Fused Pyrazoles with a ‘Click’ 1,2,3-Triazole Substituent in Position 3 Are Nanomolar CB1 Receptor Ligands
Further Information
Publication History
Received: 19 November 2014
Accepted: 12 December 2014
Publication Date:
16 January 2015 (online)
Abstract
Structural modification of the potent conformationally constrained tricyclic pyrazole CB1 ligand NESS0327 was achieved by replacing: (1) the chlorine substituent on the tricycle with a 3-fluoropropyl chain, and (2) the pyrazole 3-{[(piperidino)amino]carbonyl} substituent with a 4-substituted 1,2,3-triazole group obtained by click chemistry from an alkynyl precursor. Among the resulting compounds, two are particularly promising candidates for [18F]radiolabelling and PET imaging studies of the CB1 receptor, as they displayed K i CB1 = 62.5 nM and 42.5 nM, respectively, in the same range as that displayed by rimonabant.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379887.
- Supporting Information
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